Literature DB >> 23284376

catena-Poly[zinc-μ(3)-{3,3'-[(1,7-dioxa-4,10-diaza-cyclo-dodecane-4,10-di-yl)bis-(methyl-ene)]dibenzoato}].

C W Ingram1, L Liao, J Bacsa.   

Abstract

The Zn(II) ion in the title compound, [Zn(C(24)H(28)N(2)O(6))](n), is located on a twofold rotation axis and is at the midpoint of a crown-4 moiety of 3,3'-[(1,7-dioxa-4,10-diaza-cyclo-dodecane-4,10-di-yl)bis-(methyl-ene)]dibenzoate anion. It is octahedrally coordinated by two N atoms and two O atoms of the crown moiety from one ligand and two carboxyl-ate O atoms from two bridging intra-chain ligands. Metallomacrocyclic rings are identified in the structure. The metallomacrocycle contains two Zn(II) ions and 14 atoms from the bridging ligands. Repetition of these units gives rise to an infinite zigzag chain along [101]. C-H⋯O hydrogen bonds occur.

Entities:  

Year:  2012        PMID： 23284376      PMCID： PMC3515149          DOI： 10.1107/S1600536812043450

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For coordination polymers including metal-organic framework structures, see: Bai et al. (2012 ▶); Janiak (2003 ▶); Kitagawa et al. (2004 ▶); Li et al. (2012 ▶); Liao et al. (2012 ▶); Liu et al. (2012 ▶); O’Keeffe et al. (2000 ▶); Suh et al. (2012 ▶); Yoon et al. (2012 ▶).

Experimental

Crystal data

[Zn(C24H28N2O6)] M = 505.87 Monoclinic, a = 20.7264 (15) Å b = 8.9791 (7) Å c = 13.9745 (19) Å β = 127.200 (4)° V = 2071.5 (4) Å3 Z = 4 Cu Kα radiation μ = 2.05 mm−1 T = 173 K 0.48 × 0.14 × 0.11 mm

Data collection

Bruker D8 diffractometer with an APEXII detector Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.414, T max = 0.685 4413 measured reflections 1684 independent reflections 1538 reflections with I > 2σ(I) R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.033 wR(F 2) = 0.086 S = 1.06 1684 reflections 150 parameters H-atom parameters constrained Δρmax = 0.47 e Å−3 Δρmin = −0.21 e Å−3 Data collection: APEX2 (Bruker, 2011 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: OLEX2 (Dolomanov et al., 2009 ▶); software used to prepare material for publication: OLEX2. Click here for additional data file. Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812043450/mw2087sup1.cif Click here for additional data file. Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812043450/mw2087Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
[Zn(C24H28N2O6)]F(000) = 1056
Mr = 505.87Dx = 1.622 Mg m−3
Monoclinic, C2/cCu Kα radiation, λ = 1.54184 Å
a = 20.7264 (15) ÅCell parameters from 3719 reflections
b = 8.9791 (7) Åθ = 4.0–67.7°
c = 13.9745 (19) ŵ = 2.05 mm−1
β = 127.200 (4)°T = 173 K
V = 2071.5 (4) Å3Column, colourless
Z = 40.48 × 0.14 × 0.11 mm
Bruker D8 diffractometer with an APEXII detector1684 independent reflections
Radiation source: sealed tube1538 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.029
Detector resolution: 512 pixels mm-1θmax = 65.1°, θmin = 5.4°
φ and ω scans with a narrow frame widthh = −24→18
Absorption correction: multi-scan (SADABS; Bruker, 2008)k = −10→10
Tmin = 0.414, Tmax = 0.685l = −14→15
4413 measured reflections
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.033Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.086H-atom parameters constrained
S = 1.06w = 1/[σ2(Fo2) + (0.0475P)2 + 2.6887P] where P = (Fo2 + 2Fc2)/3
1684 reflections(Δ/σ)max < 0.001
150 parametersΔρmax = 0.47 e Å−3
0 restraintsΔρmin = −0.21 e Å−3
Experimental. Absorption correction: SADABS (Bruker-AXS, 2008) was used for absorption correction. R(int) was 0.0732 before and 0.0388 after correction. The ratio of minimum to maximum transmission is 0.6049. The λ/2 correction factor is not present.
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2> σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.
xyzUiso*/Ueq
Zn10.000000.05167 (4)0.250000.0179 (1)
O10.07654 (9)0.18185 (17)0.24895 (14)0.0224 (4)
O2−0.00673 (9)0.3592 (2)0.11945 (15)0.0325 (5)
O30.55621 (9)0.63747 (19)0.71322 (13)0.0254 (4)
N10.39893 (11)0.5343 (2)0.56752 (16)0.0193 (5)
C10.06066 (13)0.3070 (3)0.19486 (19)0.0213 (6)
C20.13504 (13)0.3887 (2)0.22567 (19)0.0196 (6)
C30.21035 (13)0.3696 (2)0.33678 (19)0.0201 (6)
C40.28068 (13)0.4328 (2)0.36223 (19)0.0200 (6)
C50.36142 (13)0.4041 (2)0.48377 (19)0.0206 (6)
C60.33847 (13)0.5969 (3)0.58104 (19)0.0232 (6)
C70.37416 (14)0.7072 (3)0.6834 (2)0.0258 (7)
C80.42804 (14)0.6450 (3)0.52237 (19)0.0247 (6)
C90.49985 (14)0.7382 (3)0.6195 (2)0.0255 (7)
C100.27460 (13)0.5139 (3)0.2717 (2)0.0229 (6)
C110.19960 (14)0.5358 (3)0.1619 (2)0.0235 (7)
C120.12995 (13)0.4758 (2)0.13890 (19)0.0204 (6)
H30.213900.311900.396800.0240*
H5A0.353700.323300.524200.0250*
H5B0.400200.367500.469900.0250*
H6A0.313300.514200.594500.0280*
H6B0.295200.647000.505200.0280*
H7A0.389800.800300.664200.0310*
H7B0.334200.731800.698100.0310*
H8A0.382700.712700.465700.0300*
H8B0.443400.591500.476900.0300*
H9A0.525100.789400.586900.0310*
H9B0.482200.814300.650500.0310*
H100.321900.554100.285300.0280*
H110.196000.593000.101600.0280*
H120.078800.494000.064100.0250*
U11U22U33U12U13U23
Zn10.0119 (2)0.0195 (2)0.0178 (2)0.00000.0066 (2)0.0000
O10.0161 (7)0.0227 (8)0.0279 (8)−0.0020 (6)0.0131 (7)0.0024 (6)
O20.0159 (8)0.0391 (10)0.0287 (9)−0.0006 (7)0.0063 (7)0.0110 (7)
O30.0178 (8)0.0244 (8)0.0205 (7)−0.0034 (6)0.0045 (7)0.0021 (6)
N10.0142 (9)0.0212 (10)0.0184 (9)0.0003 (7)0.0077 (8)0.0012 (7)
C10.0181 (11)0.0250 (12)0.0170 (10)−0.0017 (9)0.0086 (9)−0.0012 (9)
C20.0181 (11)0.0191 (11)0.0197 (10)0.0019 (8)0.0104 (9)−0.0012 (8)
C30.0198 (11)0.0198 (11)0.0183 (10)0.0003 (9)0.0103 (9)0.0006 (8)
C40.0174 (11)0.0195 (11)0.0197 (10)0.0005 (8)0.0094 (9)−0.0016 (8)
C50.0154 (10)0.0218 (11)0.0192 (10)0.0000 (8)0.0077 (9)0.0007 (8)
C60.0129 (10)0.0291 (12)0.0198 (10)0.0051 (9)0.0058 (9)0.0020 (9)
C70.0181 (11)0.0279 (12)0.0226 (11)0.0082 (9)0.0077 (9)0.0021 (9)
C80.0207 (11)0.0264 (12)0.0190 (10)−0.0014 (9)0.0078 (10)0.0043 (9)
C90.0217 (11)0.0237 (12)0.0234 (11)−0.0022 (9)0.0096 (10)0.0059 (9)
C100.0198 (11)0.0249 (11)0.0233 (11)−0.0033 (9)0.0126 (10)−0.0020 (9)
C110.0244 (12)0.0239 (12)0.0208 (11)−0.0004 (9)0.0130 (10)0.0022 (9)
C120.0170 (11)0.0197 (11)0.0180 (10)0.0021 (8)0.0071 (9)−0.0008 (8)
Zn1—O11.978 (2)C6—C71.515 (3)
Zn1—O1i1.978 (2)C8—C91.522 (4)
Zn1—O3ii2.2869 (19)C10—C111.388 (4)
Zn1—N1ii2.2422 (19)C11—C121.384 (4)
Zn1—O3iii2.2869 (19)C3—H30.9500
Zn1—N1iii2.2422 (19)C5—H5A0.9900
O1—C11.281 (3)C5—H5B0.9900
O2—C11.225 (3)C6—H6A0.9900
O3—C91.431 (3)C6—H6B0.9900
O3—C7iv1.429 (3)C7—H7A0.9900
N1—C51.497 (3)C7—H7B0.9900
N1—C61.486 (4)C8—H8A0.9900
N1—C81.487 (4)C8—H8B0.9900
C1—C21.516 (4)C9—H9A0.9900
C2—C31.395 (3)C9—H9B0.9900
C2—C121.392 (3)C10—H100.9500
C3—C41.395 (4)C11—H110.9500
C4—C51.521 (3)C12—H120.9500
C4—C101.398 (3)
O1—Zn1—O1i107.54 (8)N1—C8—C9114.72 (19)
O1—Zn1—O3ii163.85 (7)O3—C9—C8106.6 (2)
O1—Zn1—N1ii90.57 (8)C4—C10—C11120.2 (3)
O1—Zn1—O3iii85.26 (7)C10—C11—C12121.0 (2)
O1—Zn1—N1iii113.40 (8)C2—C12—C11119.8 (2)
O1i—Zn1—O3ii85.26 (7)C2—C3—H3119.00
O1i—Zn1—N1ii113.40 (8)C4—C3—H3119.00
O1i—Zn1—O3iii163.85 (7)N1—C5—H5A108.00
O1i—Zn1—N1iii90.57 (8)N1—C5—H5B108.00
O3ii—Zn1—N1ii75.01 (7)C4—C5—H5A108.00
O3ii—Zn1—O3iii84.09 (7)C4—C5—H5B108.00
O3ii—Zn1—N1iii75.37 (7)H5A—C5—H5B107.00
O3iii—Zn1—N1ii75.37 (7)N1—C6—H6A109.00
N1ii—Zn1—N1iii139.73 (7)N1—C6—H6B109.00
O3iii—Zn1—N1iii75.01 (7)C7—C6—H6A109.00
Zn1—O1—C1126.99 (19)C7—C6—H6B109.00
C7iv—O3—C9114.52 (19)H6A—C6—H6B108.00
Zn1ii—O3—C9115.48 (17)C6—C7—H7A110.00
Zn1ii—O3—C7iv116.02 (14)C6—C7—H7B110.00
C5—N1—C6108.4 (2)H7A—C7—H7B109.00
C5—N1—C8110.03 (19)O3iv—C7—H7A110.00
Zn1ii—N1—C5107.87 (12)O3iv—C7—H7B110.00
C6—N1—C8113.0 (2)N1—C8—H8A109.00
Zn1ii—N1—C6105.39 (13)N1—C8—H8B109.00
Zn1ii—N1—C8111.90 (16)C9—C8—H8A109.00
O1—C1—O2126.6 (3)C9—C8—H8B109.00
O1—C1—C2113.7 (2)H8A—C8—H8B108.00
O2—C1—C2119.6 (2)O3—C9—H9A110.00
C1—C2—C3121.2 (2)O3—C9—H9B110.00
C1—C2—C12119.7 (2)C8—C9—H9A110.00
C3—C2—C12118.9 (3)C8—C9—H9B110.00
C2—C3—C4121.8 (2)H9A—C9—H9B109.00
C3—C4—C5119.4 (2)C4—C10—H10120.00
C3—C4—C10118.2 (2)C11—C10—H10120.00
C5—C4—C10122.4 (3)C10—C11—H11119.00
N1—C5—C4116.19 (17)C12—C11—H11120.00
N1—C6—C7113.6 (2)C2—C12—H12120.00
O3iv—C7—C6106.6 (2)C11—C12—H12120.00
O1i—Zn1—O1—C1−36.0 (2)O1—C1—C2—C3−28.4 (3)
N1ii—Zn1—O1—C1−150.78 (19)O1—C1—C2—C12146.7 (2)
O3iii—Zn1—O1—C1133.96 (19)O2—C1—C2—C3155.2 (2)
N1iii—Zn1—O1—C162.5 (2)O2—C1—C2—C12−29.7 (4)
Zn1—O1—C1—O2−11.7 (4)C1—C2—C3—C4173.8 (2)
Zn1—O1—C1—C2172.18 (15)C12—C2—C3—C4−1.3 (3)
C7iv—O3—C9—C8−176.1 (2)C1—C2—C12—C11−172.2 (2)
Zn1ii—O3—C9—C8−37.4 (3)C3—C2—C12—C113.0 (3)
C9—O3—C7iv—C6iv160.4 (2)C2—C3—C4—C5−178.2 (2)
C6—N1—C5—C453.7 (3)C2—C3—C4—C10−1.7 (3)
C8—N1—C5—C4−70.4 (3)C3—C4—C5—N1−110.1 (2)
Zn1ii—N1—C5—C4167.3 (2)C10—C4—C5—N173.5 (3)
C5—N1—C6—C7167.45 (19)C3—C4—C10—C113.0 (4)
C8—N1—C6—C7−70.3 (2)C5—C4—C10—C11179.4 (2)
Zn1ii—N1—C6—C752.2 (2)N1—C6—C7—O3iv−49.9 (3)
C5—N1—C8—C9−151.4 (2)N1—C8—C9—O345.1 (3)
C6—N1—C8—C987.3 (3)C4—C10—C11—C12−1.3 (4)
Zn1ii—N1—C8—C9−31.5 (3)C10—C11—C12—C2−1.7 (4)
D—H···AD—HH···AD···AD—H···A
C5—H5A···O1ii0.992.573.224 (3)124
C12—H12···O2v0.952.433.256 (3)145
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A D—HH⋯A D⋯A D—H⋯A
C5—H5A⋯O1i 0.992.573.224 (3)124
C12—H12⋯O2ii 0.952.433.256 (3)145

Symmetry codes: (i) ; (ii) .

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Review 4.  Metal-organic frameworks for separations.

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5.  A short history of SHELX.

Authors:  George M Sheldrick
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  5 in total
  1 in total

1.  catena-Poly[{μ3-3,3'-[(1,7-dioxa-4,10-di-aza-cyclo-dodecane-4,10-di-yl)bis-(methyl-ene)]dibenzoato}cobalt(II)].

Authors:  Liang Liao; Conrad W Ingram; John Bacsa; Cass Parker
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2013-12-18
  1 in total

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